112121-72-9Relevant academic research and scientific papers
Exceptionally simple homologation of protected α- to β-amino acids in the presence of silica gel
Koch, Karen,Podlech, Joachim
, p. 2789 - 2794 (2005)
The Wolff rearrangement of α-amino acid-derived diazoketones is simply achieved by gentle warming in a ethyl acetate/silica gel slurry containing catalytic amounts of silver trifluoroacetate. Without workup (not counting filtration and evaporation) the pr
MODULATORS OF HISTONE METHYLTRANSFERASE, AND METHODS OF USE THEREOF
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, (2012/06/30)
Disclosed are compounds, pharmaceutical compositions containing the compounds, and the uses of the compounds and compositions as modulators of histone methyltransferases, and for treating diseases influenced by modulation of histone methyltransferase activity.
Total synthesis of N14-desacetoxytubulysin H
Wipf, Peter,Wang, Zhiyong
, p. 1605 - 1607 (2008/02/03)
Equation presented The N14-desacetoxy analogue of tubulysin H was prepared in 20 steps and 2.1% overall yield. Our strategy features a thiazole anion addition to assemble the tubuvaline residue at the C(10)-C(11) bond, as well as acylations at
Organocatalytic asymmetric mannich reactions with JV-Boc and JV-Cbz protected α-amido sulfones (Boc: Tert-butoxycarbonyl, Cbz: Benzyloxycarbonyl)
Marianacci, Olindo,Micheletti, Gabriele,Bernardi, Luca,Fini, Francesco,Fochi, Mariafrancesca,Pettersen, Daniel,Sgarzani, Valentina,Ricci, Alfredo
, p. 8338 - 8351 (2008/04/01)
Different malonates and βketoesters can react with N-tert-butoxycarbonyl- (N-Boc) and N-benzyloxycarbonyl- (N-Cbz) protected α-amido sulfones in an organocatalytic asymmetric Mannich-type reaction. The reaction makes use of a simple and easily obtained ph
Phase-transfer-catalyzed enantioselective Mannich reaction of malonates with α-amido sulfones
Fini, Francesco,Bernardi, Luca,Herrera, Raquel P.,Pettersen, Daniel,Ricci, Alfrede,Sgarzani, Valentina
, p. 2043 - 2046 (2007/10/03)
The highly enantioselective reaction between in situ generated, Cbz-protected azomethines and malonates in the presence of 150 mol% of potassium carbonate (50% w/w) and 1 mol% of quinine-derived quaternary ammonium bromides as phase-transfer organocatalys
An allyltitanium derived from acrolein 1,2-dicyclohexylethylene acetal and (η2-propene)Ti(o-i-Pr)2 as a chiral propionaldehyde homoenolate equivalent that reacts with imines with excellent stereoselectivity. An efficient and practical access to optically active γ-amino carbonyl compounds
Okamoto,Teng,Fujii,Takayama,Sato
, p. 3462 - 3471 (2007/10/03)
A chiral allyltitanium compound 2, prepared in situ by the reaction of optically active acrolein 1,2-dicyclohexylethylene acetal (3) with (η2-propene)Ti(O-i-Pr)2 (1), reacts with a variety of acyclic and cyclic imines 4 in a regiospecific way to afford α-addition products 5 as a mixture of the E- and Z-isomers in good combined yield, where the former is predominant in a ratio of 92: 8 to >95:5. The mixture of (E)- and (Z)-5 and pure (E)-5 which could be isolated in several cases were respectively converted to the corresponding β-amino ester 6 to confirm the absolute configuration and enantiomeric purity. The ee of the newly formed asymmetric center of 5 is more than 78% for the mixture of (E)- and (Z)-5 and more than 96% for pure (E)-5. By taking advantage of the versatility of the vinyl ether moiety in 5, optically active γ-amino aldehydes 8, γ-amino aldehyde acetals 7 and 10, γ-amino acids 9, β-amino esters 6, and pyrrolidinoisoquinolines 12 were readily prepared. In the reaction of 2 with optically active α-silyloxyimine 4n, remarkable double stereodifferentiation was observed; thus, the reaction of 2 derived from (S,S)- or (R,R)-3 provided syn- and anti-5n in a ratio of 55:45 or 0:100, respectively. Meanwhile, the stereochemistry of the product in the reaction of 2 with β-silyloxyimine 4o was controlled mainly by 2. Thus, the reaction of β-silyloxyimine 14 with 2 derived from 1 and (R,R)-3 afforded γ-silyloxyimine 15 with 92% diastereoselectivity, from which 4-amino6-hydroxypentadecanal dimethyl acetal (13), a key intermediate for the synthesis of batzelladine D, was synthesized.
Chiral oxime ethers in asymmetric synthesis. Part 4. Asymmetric synthesis of N-protected amines and β-amino acids by the addition of organometallic reagents to ROPHy/SOPHy-derived aldoximes
Hunt, James C. A.,Lloyd, Cephas,Moody, Christopher J.,Slawin, Alexandra M. Z.,Takle, Andrew K.
, p. 3443 - 3454 (2007/10/03)
Addition of organolithium or Grignard reagents to (R)- or (S)-O-(1-phenylbutyl)aldehyde oximes 1 in the presence of boron trifluoride-diethyl ether results in the formation of hydroxylamines 2 in good to excellent diastereoselectivity. Subsequent cleavage of the N-O bond with zinc-acetic acid-ultrasound, and carbamate formation, gives N-protected amines 3 in good enantiomeric purity (77-100% ee). When allylmagnesium bromide was used as the organometallic reagent, the resulting hydroxylamines were converted into β-amino acid derivatives 4 and γ-aminb alcohols 5. The Royal Society of Chemistry 1999.
Addition of allylmagnesium bromide to ROPHy/SOPHy aldoximes: Asymmetric synthesis of protected β-amino acids
Moody, Christopher J.,Hunt, James C. A.
, p. 733 - 734 (2007/10/03)
A new asymmetric synthesis of protected β-amino acids is described in which the key step is the diastereoselective addition of allylmagnesium bromide to O-(1-phenylbutyl) aldoximes.
1. Use of the Wolff Rearrangement of Diazo Ketones from Amino Acids as a Synthetic Method for the Formation of Oligonucleo-peptides: A Novel Approach to Chimeric Biomolecules
Guibourdenche, Christel,Seebach, Dieter,Natt, Francois
, p. 1 - 13 (2007/10/03)
Photolysis and Ag-benzoate-catalyzed decomposition of the diazo ketones 2 and 4 derived from Z-Ala-OH and Z-Ala-Ala-OH in the presence of oligonucleotide derivatives bearing at the 5′-terminus an NH2 instead of the OH group, or an aminohexyl phosphate group lead to Z-protected 3-aminobutanoyl and to Z-Ala-β-HAla derivatives, respectively (conjugates 12, 13, and 17-23, Schemes 3-5). In solution, this amide-forming acylation reaction could be realized only with oligomers containing up to 8 unprotected nucleotide building blocks (Schemes 3 and 4). With the analogous polymer-bound and protected oligonucleotide derivatives as amino nucleophiles, excellent yields were obtained with all chain lengths tested (up to 15mer, Scheme 5). The products were purified by reversed-phase HPLC and characterized by MALDI-TOF mass spectrometry (Figs. 2-4, Table 2) and by capillary gel electrophoresis (Fig. 2).
